EP0429601A1 - Von hexachloro-1,3-butadien abgeleitete silyl- und disilanyl-1,3-butadiengruppen enthaltende polymere - Google Patents

Von hexachloro-1,3-butadien abgeleitete silyl- und disilanyl-1,3-butadiengruppen enthaltende polymere

Info

Publication number
EP0429601A1
EP0429601A1 EP90908792A EP90908792A EP0429601A1 EP 0429601 A1 EP0429601 A1 EP 0429601A1 EP 90908792 A EP90908792 A EP 90908792A EP 90908792 A EP90908792 A EP 90908792A EP 0429601 A1 EP0429601 A1 EP 0429601A1
Authority
EP
European Patent Office
Prior art keywords
polymer
polymers
hydrogen
butadiyne
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
EP90908792A
Other languages
English (en)
French (fr)
Other versions
EP0429601A4 (en
Inventor
Thomas J. Barton
Sina Ijadi-Maghsoodi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of Iowa Research Foundation UIRF
Iowa State University Research Foundation ISURF
Original Assignee
University of Iowa Research Foundation UIRF
Iowa State University Research Foundation ISURF
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by University of Iowa Research Foundation UIRF, Iowa State University Research Foundation ISURF filed Critical University of Iowa Research Foundation UIRF
Publication of EP0429601A1 publication Critical patent/EP0429601A1/de
Publication of EP0429601A4 publication Critical patent/EP0429601A4/en
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
    • C04B35/515—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics
    • C04B35/56—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on carbides or oxycarbides
    • C04B35/565—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on carbides or oxycarbides based on silicon carbide
    • C04B35/571—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on carbides or oxycarbides based on silicon carbide obtained from Si-containing polymer precursors or organosilicon monomers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/60—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which all the silicon atoms are connected by linkages other than oxygen atoms

Definitions

  • the present invention relates to organosilicon polymers having recurring silylene-1,3-butadiyne units.
  • the invention relates to reaction products of hexachloro-1,3-butadiene and n- butyllithium followed by quenching with certain dichlorosilanes to provide useful polymers that have good film-forming properties, at least one of which can be pulled into fibers, all of which are thermally converted into silicon carbide with a high ceramic yield, and many of which offer attractive candidates for electrical conduction and non-linear optical properties.
  • This invention relates to silylene- and
  • disilylene-1,3-butadiyne polymers The polymers are prepared by reacting hexachloro-1,3-butadiene with n- butyllithium, followed by quenching with RR'SiCl 2 to produce silylene-1,3-butadiyne polymers or followed by quenching with ClR 2 SiSiR 2 Cl to form disilylene- 1,3-butadiyne polymers.
  • Type A polymers hereinafter referred to, from time to time, as a "Type A" polymers.
  • dichlorodimethylsilane (Me 2 SiCl 2 ) was added in a dropwise fashion over a 5 minute period.
  • GPC M w from ca. 3,000-100,000 with the maximum at ca. 20,000.
  • These polymers are excellent candidates for nonlinear optical materials. Heating these polymers up to 1,300oC while monitoring by X-ray powder diffraction revealed only the 111,220 and 311 lines of -silicon carbide.
  • Type A polymers were prepared using the exact procedure earlier described.
  • R R' equals phenyl or methyl, and mixed R's, wherein R is phenyl and R' is methyl.
  • R is phenyl and R' is methyl.
  • Each of these was characterized in the manner given above, each was formed in high yield, and had molecular weights within the range herein specified. Only those polymers which had at least one phenyl substituent on silicon pulled fibers of good quality, and these polymers also produced the best quality films.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Ceramic Engineering (AREA)
  • Materials Engineering (AREA)
  • Structural Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Silicon Polymers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
EP19900908792 1989-05-16 1990-05-16 Silyl- and disilanyl-1,3-butadiyne polymers from hexachloro-1,3-butadiene Ceased EP0429601A4 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/352,825 US4965332A (en) 1989-05-16 1989-05-16 Silyl- and disilanyl-1,3-butadiyne polymers from hexachloro-1,3-butadiene
US352825 1999-07-13

Publications (2)

Publication Number Publication Date
EP0429601A1 true EP0429601A1 (de) 1991-06-05
EP0429601A4 EP0429601A4 (en) 1992-01-15

Family

ID=23386662

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19900908792 Ceased EP0429601A4 (en) 1989-05-16 1990-05-16 Silyl- and disilanyl-1,3-butadiyne polymers from hexachloro-1,3-butadiene

Country Status (5)

Country Link
US (1) US4965332A (de)
EP (1) EP0429601A4 (de)
JP (1) JPH03502712A (de)
CA (1) CA2016947A1 (de)
WO (1) WO1990014381A1 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5241029A (en) * 1992-01-07 1993-08-31 Iowa State University Research Foundation, Inc. Diorganosilacetylene-alt-diorganosilvinylene polymers and a process of preparation
US5243060A (en) * 1992-04-10 1993-09-07 Iowa State University Research Foundation, Inc. Silylene-diethynyl-arylene polymers having liquid crystalline properties
US5563181A (en) * 1995-05-09 1996-10-08 The United States Of America As Represented By The Secretary Of The Navy Siloxane unsaturated hydrocarbon based thermosetting polymers
US5874514A (en) * 1995-05-09 1999-02-23 Us Navy Siloxane unsaturated hydrocarbon based polymers
US6784270B1 (en) 2002-09-26 2004-08-31 The United States Of America As Represented By The Secretary Of The Navy Polymer containing borate and alkynyl groups
US6767981B1 (en) 2002-09-26 2004-07-27 The United States Of America As Represented By The Secretary Of The Navy Thermoset and ceramic containing silicon and boron
CN100504565C (zh) * 2006-07-28 2009-06-24 中国科学院理化技术研究所 非线性光学活性有机硅聚合物及其制备方法和用途

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2037343A1 (de) * 1969-07-30 1971-02-18 Midland Silicones Ltd , Reading, Berkshire (Großbritannien) Organosiliciumverbindungen und deren Polymerisate sowie Verfahren zur Herstel lung beider
FR2646162A1 (fr) * 1989-04-21 1990-10-26 Rhone Poulenc Chimie Procede de preparation de polysilylpolyynes et polymeres obtenus a l'issue de ce procede
GB2233660A (en) * 1989-06-22 1991-01-16 Dow Corning Method of making organosilbutadiyne polymers

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3660449A (en) * 1970-03-03 1972-05-02 Owens Illinois Inc Reaction products of silicon monoxide and acetylenes and methods of preparing the same
US3700714A (en) * 1971-06-24 1972-10-24 Stephen B Hamilton Curable compositions
SU802313A1 (ru) * 1978-08-30 1981-02-07 Институт Нефтехимического Синтезаим. A.B.Топчиева Ah Cccp Высокомолекул рный кристалли-чЕСКий пОлиМЕР дл бЕНзОСТОйКиХпРОКлАдОК и СпОСОб ЕгО пОлучЕНи
US4260780A (en) * 1979-11-27 1981-04-07 The United States Of America As Represented By The Secretary Of The Air Force Phenylmethylpolysilane polymers and process for their preparation
US4276424A (en) * 1979-12-03 1981-06-30 Petrarch Systems Methods for the production of organic polysilanes
FR2564470B1 (fr) * 1984-05-18 1987-01-02 Rhone Poulenc Spec Chim Resine organosilicique a motifs disilaniques et a proprietes thermomecaniques ameliorees et en outre utilisables notamment pour l'hydrofugation du batiment
US4800221A (en) * 1987-08-25 1989-01-24 Dow Corning Corporation Silicon carbide preceramic polymers
US4923949A (en) * 1988-08-03 1990-05-08 Kanegafuchi Chemical Industry Co., Ltd. Ethynylene-disilanylene copolymers and method of preparing same

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2037343A1 (de) * 1969-07-30 1971-02-18 Midland Silicones Ltd , Reading, Berkshire (Großbritannien) Organosiliciumverbindungen und deren Polymerisate sowie Verfahren zur Herstel lung beider
FR2646162A1 (fr) * 1989-04-21 1990-10-26 Rhone Poulenc Chimie Procede de preparation de polysilylpolyynes et polymeres obtenus a l'issue de ce procede
GB2233660A (en) * 1989-06-22 1991-01-16 Dow Corning Method of making organosilbutadiyne polymers

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 68, no. 18, 29th April 1968, page 7602, abstract no. 78657t, Columbus, Ohio, US; L.K. LUNEVA et al.: "Synthesis of organosilicon and organogermanium polymers with diacetylenic groups in the chain", & IZV. AKAD. NAUK SSSR, SER. KHIM. 1968(1), 170-4 *
INTERNATIONAL POLYMER SCIENCE AND TECHNOLOGY, vol. 9, no. 2, 1982, pages T51-T53, Shrewsbury, GB; A.M. FOMIN et al.: "Electrical properties of silicon-acetylene and germanium-acetylene polymers" *
JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 381, no. 3, 30th January 1990, pages C57-C59, Lausanne, CH; M. ISHIKAWA et al.: "Polymeric organosilicon system. VIII. Synthesis of polyÄ(disilanylene)diethynyleneÜ with highly conducting properties" *
See also references of WO9014381A1 *

Also Published As

Publication number Publication date
WO1990014381A1 (en) 1990-11-29
JPH0583571B2 (de) 1993-11-26
CA2016947A1 (en) 1990-11-16
JPH03502712A (ja) 1991-06-20
US4965332A (en) 1990-10-23
EP0429601A4 (en) 1992-01-15

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